Chicago’s skyline rises like a steel symphony above Lake Michigan, but its real soundtrack is the buzz of neighborhoods, museums, parks, and theaters that have been delighting visitors for well over a century. Whether you’re tracing the footsteps of 1893 World’s Fair dreamers or clinking glasses in a 21st-century rooftop bar, the Windy City mixes history and innovation at every turn.
This guide ranks the 21 Things to Do in Chicago —from blockbuster sights on every postcard to local favorites where true Chicago flavor lingers. Lace up your walking shoes, charge your phone for photo ops, and get ready to meet a city that never runs out of surprises.
Millennium Park & “Cloud Gate”
Opened in July 2004, Millennium Park transformed a tangle of rail tracks into Chicago’s outdoor living room and now draws about 25 million visitors a year. Snap the obligatory selfie beside Anish Kapoor’s mirrored “Bean” (installed 2006), then sprawl on the lawn for free concerts at the Frank Gehry-designed Jay Pritzker Pavilion. Winter swaps lawn blankets for skates on the Ice Ribbon, while Crown Fountain’s video portraits soak summertime crowds. Seasonal pop-up art, gardens, and Instagram-ready skyline views keep surprises coming. Few public spaces pack so much Chicago spirit into 21 acres.
The Art Institute of Chicago
The stone lions have guarded the Art Institute of Chicago since 1893, ushering visitors into a Beaux-Arts palace filled with more than 300,000 works spanning 5,000 years. Stand face-to-brushstroke with Grant Wood’s American Gothic, lose yourself in Monet’s luminous water-lily panels, or linger among Thorne Miniature Rooms. The Renzo Piano-designed Modern Wing (2009) adds 264,000 square feet of light-washed galleries and a rooftop bridge linking to Millennium Park. With Asian scrolls, African masks, and a sublime collection of Impressionism, the museum rewards both first-timers and lifelong art nerds. Plan on at least half a day—curating your own mini-tour is an art form in itself.
Navy Pier
Debuting in 1916 as Municipal Pier No. 2, Navy Pier has morphed from freight dock to lakefront playground. Families queue for the 196-foot Centennial Wheel, ride the historic carousel, and catch IMAX blockbusters while lake breezes whip their hair. Boat cruises launch to skyline backdrops, and fireworks burst over Lake Michigan every Wednesday and Saturday from Memorial Day through Labor Day. Even in January, palms rustle beneath the glass-domed Crystal Gardens while ice sculptures sparkle outside. After a century of reinventions, the pier proves nostalgia and neon can share the same boardwalk.
Willis Tower Skydeck & The Ledge
When the 110-story Willis Tower (née Sears, 1973) opened, it claimed the title of world’s tallest building—Chicago’s ultimate “top this” moment. A 60-second elevator ride whisks you to the Skydeck on the 103rd floor, where the glass-bottom Ledge boxes (added 2009) dangle you 1,353 feet above Wacker Drive. On clear days you can spot four states, and sunset gilds the city grid like molten copper. Interactive exhibits reveal elevator engineering tricks and dizzying construction photos. The bravest step onto the Ledge at night, when Chicago’s lights glow like a circuit board beneath your feet.
Chicago River Architecture Cruise
Few classrooms rival a Chicago River Architecture Cruise for storytelling power. In 90 minutes, docents unpack 150 years of skyline rivalry—from Daniel Burnham’s classical towers to Jeanne Gang’s 2019 rippling St. Regis. Steel bridges clatter overhead, kayakers bob beside tour boats, and riverwalk cafés bustle with lunchtime chatter. You’ll learn why the river’s flow was famously reversed in 1900 and how a polluted industrial channel became a glittering urban “second shoreline.” Bring layers—the canyon breeze can bite even in July.
Shedd Aquarium
Land-locked Chicagoans first glimpsed saltwater wonders when Shedd Aquarium opened in 1930 as the world’s largest indoor aquarium. Today its 32,000 animals include graceful belugas in the Abbott Oceanarium and tarpon swirling through the Caribbean Reef rotunda. Wild Reef, unveiled in 2003, plunges you into a Philippine-style shark habitat via an 11-foot-deep acrylic tunnel. Conservation chats demystify coral-bleaching and microplastics before you meet rockhopper penguins with mohawk crests. Pair the Shedd with the neighboring Adler Planetarium or Field Museum for a science-trifecta day.
Field Museum of Natural History
Born from the 1893 World’s Columbian Exposition, the Field Museum moved to its neo-classical lakefront home in 1921. Visitors make a beeline for “SUE,” the world’s most complete Tyrannosaurus rex, relocated to a purpose-built suite in 2018 with atmospheric lighting and extra fossils. Upstairs, “Inside Ancient Egypt” guides you through a 4,000-year-old tomb passage before depositing you amid painted coffins and friendly mummies. Rotating blockbusters—think Maori taonga or Antarctic dinosaurs—keep locals renewing memberships. With 40 million specimens in storage, the Field reminds us curiosity is humanity’s oldest survival tool.
Museum of Science and Industry
Housed in the last surviving building from the 1933 Century of Progress Fair, the Museum of Science and Industry turns learning into an adrenaline rush. Descend into a rumbling coal mine, walk through a tornado of vapor, or slip inside the U-505, the only German U-boat on U.S. soil. Baby chicks peck free in the genetics lab, and a full-size 727 airplane hangs overhead. Each December, “Christmas Around the World” decorates 50-plus trees in cultural finery—a tradition since WWII. This is where future engineers realize science can make their hearts race.
The Magnificent Mile
Michigan Avenue’s north stretch, christened The Magnificent Mile in 1947, is equal parts retail runway and architectural hall-of-fame. Flagship stores lure shoppers seven stories deep, while 1920s icons like the terracotta Wrigley Building and neo-Gothic Tribune Tower beg neck-stretching admiration. Street musicians riff on jazz, deep-dish joints vie with Michelin-starred plates, and window displays glow after dark like vintage travel-reel frames. Peek at the 1869 Chicago Water Tower—the rare Great Fire survivor—before splurging at designer boutiques further north. No wonder this stretch draws nearly 20 million pedestrians each year.
Wrigley Field & Wrigleyville
Baseball nostalgia perfumes ivy-draped Wrigley Field, MLB’s second-oldest stadium (1914). Even off-days hum with fans snapping selfies beneath the red marquee, rooftop bleachers grilling brats, and “Go Cubs Go” drifting from Sheffield Avenue bars. Inside, hand-turned scoreboards resist digital takeover, and beer vendors still hawk Old Style. The surrounding Wrigleyville neighborhood erupts in blue when the Cubs win, spilling celebrations onto Clark Street. Grab a Chicago-style hot dog “dragged through the garden,” and you’re honorary North Sider for the day.
360 Chicago at the John Hancock Center
Soaring 1,128 feet since 1969, the John Hancock’s 94th-floor observatory rebranded as 360 Chicago in 2014. Brave souls lean outward on TILT, a moving glass platform that angles visitors over buzzing Michigan Avenue. Clear-day vistas reveal four states and the sail-speckled blue of Lake Michigan. Stay for sunset, when Navy Pier fireworks pop like confetti beneath your toes, then toast the view with a craft cocktail at Bar 94. It’s a high-altitude love letter to Chicago’s vertical ambitions.
Lincoln Park Zoo
Founded in 1868 and proudly free, Lincoln Park Zoo squeezes global wildlife into 35 leafy acres. Orangutans swing in a sky-trail habitat, while polar bears plunge into icy pools shadowed by skyscrapers. Summer’s lush gardens morph into a winter wonderland each December when ZooLights strings millions of LEDs under snowy branches. Conservation scientists work behind the scenes on everything from ape cognition to prairie restoration. A stroll here proves “urban jungle” can be literal and figurative at once.
Grant Park & Buckingham Fountain
Dubbed “Chicago’s Front Yard,” Grant Park’s grand centerpiece is rococo Buckingham Fountain, donated in 1927 by philanthropist Kate Buckingham. The fountain launches a 150-foot jet every 20 minutes in summer, backed by synchronized lights and music after dusk. Grant Park has hosted everything from Pope John Paul II’s 1979 Mass to Barack Obama’s 2008 victory rally and Lollapalooza since 2005. Spring paints the promenades with 10,000 tulips; autumn turns trees into fiery confetti. All year, locals jog the lakefront path while gulls wheel overhead.
The Chicago Theatre
When its glitzy marquee first lit State Street in 1921, The Chicago Theatre declared that vaudeville had found a palace. Inside, a sweeping French-Baroque lobby drips with gilt and crystal, while a 60-foot triumphal arch frames the stage. Frank Sinatra crooned here in 1957, Prince rocked it in 2012, and Netflix comedy specials keep the spotlight hot today. Tours dish backstage secrets—including how the venue dodged demolition in 1986. Leaving beneath the neon sign, you feel part of Chicago showbiz lineage stretching a full century.
Garfield Park Conservatory
Landscape architect Jens Jensen called the Garfield Park Conservatory “landscape art under glass” when it opened in 1908, and its 600 plant species still stun. The Fern Room recreates Illinois pre-glacial forest, while the Desert House bathes cacti in year-round sun. After a 2011 glass-roof restoration, the Palm House’s 65-foot dome feels like stepping onto a tropical movie set. Seasonal flower shows—especially the Spring Display—turn gray February days into fragrant bursts of color. Best of all, admission is donation-based.
Chicago Cultural Center
Opened in 1897 as the city’s first main library, the Chicago Cultural Center dazzles with not one but two stained-glass domes, including a 38-foot Tiffany masterpiece—the world’s largest. Mosaic-marble staircases gleam under natural light, and free classical concerts resonate in the Grand Army of the Republic Hall each Wednesday. Rotating art exhibitions spotlight Chicago neighborhoods, while lectures unpack everything from poetry to urban planning. The building even moonlit as Gotham Courthouse in The Dark Knight (2008). Rainy-day refuge never felt so regal.
Pilsen Murals & National Museum of Mexican Art
Chicago’s Mexican-American heart beats loudest in Pilsen, where 1970s Chicano activists painted political murals that still blaze along 16th Street. Duck into the National Museum of Mexican Art (opened 1987) to explore 10,000 objects spanning pre-Columbian clay to contemporary graphic design. Day-of-the-Dead exhibits each fall fill galleries with marigolds and papel picado. Outside, cafés scent sidewalks with cinnamon-spiked champurrado, and Sunday park vendors grill elotes beside break-dancing teens. Few neighborhoods wear cultural pride as vividly.
Chinatown & Ping Tom Memorial Park
Chicago’s original Chinatown outgrew downtown and migrated south to Cermak Road in 1912; today a red-pillared gateway welcomes new generations. Dim-sum carts clatter at Phoenix Restaurant, and the nine-dragon wall (2003) replicates Qing-dynasty porcelain brick for brick. Riverside Ping Tom Memorial Park, opened in stages from 1999, frames skyline selfies with weeping willows and dragon-boat races. Lunar-New-Year lantern parades light the streets in mid-winter gloom. Here, heritage and hustle share the same dumpling-steamed air.
Hyde Park & the DuSable Museum of African American History
Home to the University of Chicago since 1890, Hyde Park blends neo-Gothic spires with Nobel-prize labs where 1942’s first self-sustaining nuclear reaction rewrote physics. The DuSable Museum, founded in 1961 by artist Margaret Burroughs, traces Black history from 18th-century fur trader Jean Baptiste Point du Sable to Barack Obama’s presidency. Jazz lounges, bookstores, and Promontory Point picnics give weekends a scholarly yet laid-back vibe. Frank Lloyd Wright’s Robie House adds Prairie-style brilliance to leafy streets. Stay past twilight to watch downtown twinkle across lake water Henry Moore once called “liquid silver.”
The 606 (Bloomingdale Trail)
Opened in 2015, The 606 repurposed an elevated railroad into a 2.7-mile linear park linking Bucktown, Wicker Park, Humboldt Park, and Logan Square. Joggers and cyclists zip past murals, community gardens, and pocket parks every few blocks. Evening runs catch sunsets dipping behind rusted freight bridges; winter sees cross-country skiers tracing silent lines where locomotives once thundered. Installations like Luftwerk’s color-shifting lights turn the trail into public art after dark. It’s Chicago’s version of the High Line—more neighborhood-gritty, less tourist-glossy, equally addicting.
Andersonville’s Swedish Heritage & Indie Scene
Originally settled by Swedish farmers in the 1850s, Andersonville flaunts its roots with the blue-and-yellow façade of the Swedish American Museum (opened 1976) and the neon fish sign outside Simon’s Tavern (since Prohibition). Clark Street boutiques champion LGBTQ+ pride, vintage furniture, and small-batch coffee that could headline any hipster crawl. Each June, Midsommarfest lines the avenue with folk dancers twirling around a maypole while herring plates and craft beer fuel the party. Winter’s Julmarknad holiday market swaps flower crowns for glögg and roasted almonds. Indie spirit and Scandinavian soul blend as smoothly as a cardamom latte.
